The integration of socio-economic and environmental objectives is a major challenge in developing strategies for sustainable landscapes. We investigated associations between socio-economic variables, landscape metrics and measures of forest condition in the context of Portugal. The main goals of the study were to 1) investigate relationships between forest conditions and measures of socio-economic development at national and regional scales, 2) test the hypothesis that a systematic variation in forest landscape metrics occurs according to the stage of socio-economic development and, 3) assess the extent to which landscape metrics can inform strategies to enhance forest sustainability. A ranking approach and statistical techniques such as Principal Component Analysis were used to achieve these objectives. Relationships between socio-economic characteristics, landscape metrics and measures of forest condition were only significant in the regional analysis of municipalities in Northern Portugal. Landscape metrics for different tree species displayed significant variations across socio-economic groups of municipalities and these differences were consistent with changes in characteristics suggested by the forest transition model. The use of metrics also helped inform place-specific strategies to improve forest management, though it was also apparent that further work was required to better incorporate differences in forest functions into sustainability planning.